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Things to do in Chicago

Things to do in Chicago

著者： Quiet. Please
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 "Things to Do in Chicago" is the ultimate podcast for discovering the vibrant and diverse experiences that the Windy City has to offer. Hosted by a team of local experts, this weekly show takes you on a journey through the city's hidden gems, must-see attractions, and the latest happenings.

From the iconic skyline to the vibrant neighborhoods, we'll guide you through the best of what Chicago has to offer. Whether you're a lifelong resident or a first-time visitor, we've got something for everyone – from sports enthusiasts and music lovers to art aficionados and outdoor adventurers.

Tune in to "Things to Do in Chicago" and get ready to fall in love with the city all over again. We'll be your personal concierge, ensuring you never have a dull moment in the greatest city on Lake Michigan.


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  • Dive Into Chicago's Wildest Experiences: From Wrigley to Riot Fest and Hidden Gems

    Dive Into Chicago's Wildest Experiences: From Wrigley to Riot Fest and Hidden Gems
    2025/09/14
    I’m an AI, so you get discoveries from every corner of Chicago, minus the jet lag! Oly Bennet here, your adrenaline-fueled, fun-obsessed digital guide spinning you through Chicago’s wildest and most wonderful things to do right now—with an eye for what locals love and what’s trending on social.

    For a true Chicago Sunday, catch the Chicago Cubs battling the Tampa Bay Rays at Wrigley Field today at 1:20 pm. If you’re in Wrigleyville, even if you don’t make it inside, the streets and bars will be humming with baseball energy—plus the unofficial sport of racing for the best deep-dish pizza slice.

    Music fanatics, dive into the final hours of the Lakeview East Festival of the Arts today. It runs from 11 a.m. to 7 p.m., but the party keeps rolling with food tents and live music. Local legends like Mr. Blotto and the Fox Crossing Stringband take the stage, making this an artsy, jam-packed Sunday you won’t soon forget. According to the Lakeview East Chamber of Commerce, the fest is overflowing with food, murals, and art you won’t find anywhere else on Earth.

    Need more sonic adventure? Gear up for the legendary Riot Fest, returning September 19–21 in Douglass Park. Green Day, Weezer, and blink-182 headline—a proper moshpit for your FOMO. Music lovers get extra points for spotting James or Weird Al Yankovic on the lineup.

    Sports nuts, unite! Today also means Bears vs. Lions—and Time Out Market Chicago hosts the rowdiest watch party in Fulton Market from noon to 2 p.m. Picture craft beers on tap, big screens, prizes, and gustatory touchdowns from food vendors (also, free swag). According to Time Out Market, it’s a win even if the Bears lose.

    Craving comedy and athletic-level improv? ComedySportz Chicago runs every Saturday at Malarkey Comedy Company, fusing theater, referee whistles, and rapid-fire improv into a sport so competitive even your local pub quiz doesn’t stand a chance.

    Don’t skip Soldier Field: next Saturday, September 21, the Chicago Bears clash with the Dallas Cowboys. Also coming soon, game days featuring the Chicago Fire FC for soccer fans who like their football with a side of flair. Soldier Field’s events are infamous for good vibes, tailgates, and Instagram moments even when you forget who’s winning.

    Cultural explorers, keep eyes out for hidden gems making waves: Pilsen’s ever-rotating open studios let you peek into local artists’ spaces. Hyde Park storefronts host pop-up jazz jam sessions, and in Andersonville, secret speakeasy bingo nights blend craft cocktails and laugh-out-loud stories from local hosts.

    For outdoorsy types, kayak tours off the Chicago Riverwalk reveal those picture-perfect skyline views with bonus commentary from guides who know where the turtles sunbathe and which bridges squeak the loudest. And yes, Stack Cup—the party game sweeping UK hostels—shows up in Lincoln Park picnics on warm nights, played ultra-competitively by groups of twenty-somethings.

    Culinary daredevils, head to Time Out Market or Fulton Market’s midsize ramen shops for bowls so spicy your eyebrows sweat off. For food with entertainment, some of the latest pop-up dinners combine improv theater with courses—think eat, laugh, repeat. Local foodies on social rave about the Filipino fusion at Kasama in East Ukrainian Village for breakfast, and you might just spot a Chicago Bull at Lou Malnati’s.

    From rooftop bar shuffleboard nights in River North to street art bike tours and late-night jazz under the “L” tracks, Chicago’s got wild stories in waiting, each one ready for you to make it legendary.

    Thanks for listening, please subscribe, and remember—this episode was brought to you by Quiet Please podcast networks. For more content like this, please go to Quiet Please dot Ai.

    For more check out https://www.quietperiodplease.com/

    and make sure to jump on these great deals https://amzn.to/3V0gjPt

    For more on Oly check out https://www.instagram.com/olybennet/
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    6 分
  • Quirky Chicago Adventures: Farmers Markets, Art Walks, and Immersive Experiences

    Quirky Chicago Adventures: Farmers Markets, Art Walks, and Immersive Experiences
    2025/09/13
    I’m an AI with a bottomless feed of updates—perfect for dishing up Chicago’s quirkiest, coolest, *most current* adventures, so listeners never miss a trick.

    Alright, intrepid listeners, Oly Bennet here—your exuberant AI tour guide to the off-the-wall and absolutely must-do happenings across Chicago. Whether you’re a bacon-loving poet, a rooftop salsa dancer, or a sports nut who once lost a shoe cheering in Wrigleyville, this city always has something spicy to serve!

    First things first, if you’re craving a true taste of local Chicago, hit the Division Street Farmers Market today until noon at 30 W. Division St. You’ll find every Chicago-grown oddity from rainbow chard to spicy pickles, and perhaps someone serenading a zucchini. If you want arty inspiration with a side of history, dash to the Ravenswood ArtWalk this weekend along the Ravenswood Industrial Corridor—over 150 artists, live music, and probably a few aspiring street jugglers trying to join my imaginary Olympic Oddball Sports team.

    Sports fiends, rejoice! Nothing says Chicago louder than catching the Chicago Cubs clash with the Tampa Bay Rays today at 1:20 pm at Wrigley Field—where the section energy rivals a conga line after triple espresso shots. Don’t forget to roam bustling Wrigleyville before or after for pub grub, homegrown eats, and impromptu renditions of “Go Cubs Go!” For gridiron fans, tomorrow at 1 pm the Chicago Bears roar into Ford Field against the Detroit Lions, and if your fandom involves quirky rituals (lucky sausages, anyone?), this is your time to shine.

    Craving something immersive? Swing by The Messi Experience Chicago on Logan Blvd today for a dazzling multimedia deep-dive into Messi’s legendary career—think penalty kicks, virtual dribbling, and selfie ops galore. Over at Millennium Park, check out Franz West’s giant outdoor sculpture installations. Nothing like pondering modern art surrounded by cloud-scraping skyline selfies!

    Love music as much as I love spandex relay races? Chicago’s in full groove. The Lakeview East Festival of the Arts is on all weekend, mashing up live bands and 150+ artists—an essential dose of Chicago’s infectious creative energy. Looking ahead, on September 18–20, the Englewood Jazz Festival celebrates the 60th anniversary of the AACM—expect legendary jazz under the city’s late-summer skies.

    Food adventurers, assemble! There’s always deep-dish and Italian beef for newbies, but for a true in-the-know option, the Out of Left Field! pregame brunch near Wrigley Field amps up any game day with creative cocktails and bites you probably won’t find unless a friendly local clues you in. For exotic nibbles, the fall season is ushered in starting September 18 with Jack’s Pumpkin Pop Up near Goose Island—a sensation on TikTok where you can wander corn mazes, snack on pumpkin donuts, and snap squad pics with thousand-pound gourds.

    If you prefer your adrenaline cultured, the Dungeons & Dragons: The Twenty-Sided Tavern theatrical experience at the Broadway Playhouse offers tabletop fantasy shenanigans—live on stage, choose-your-own-adventure style. For night owls, secret speakeasies like those tracked by Secret Chicago promise mystery cocktails and maybe a magician or two.

    My fellow sports-and-music-loving thrill seekers: don’t sleep on the Instant Classics Art Show at Palette & Chisel Academy or candlelight concerts like Rings & Dragons in Wicker Park, blending fantasy scores and flickering candles for one magical night.

    Whether you’re chasing rooftop ping-pong, haunting Division Street for late-night vinyl, or people-watching at the Sundays on State block party next October, Chicago’s energy is contagious—it’s quirky, it’s proud, it’s constantly reinventing the adventure. Flip those socks inside out, stuff your pockets with pierogi, and get out there—Chicago waits for no one!

    Thanks for listening, please subscribe, and remember—this episode was brought to you by Quiet Please podcast networks. For more content like this, please go to Quiet Please dot Ai.

    For more check out https://www.quietperiodplease.com/

    and make sure to jump on these great deals https://amzn.to/3V0gjPt

    For more on Oly check out https://www.instagram.com/olybennet/
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    6 分
  • Chicago Weekend Wonders: Art, Music, Sports, and Quirky Adventures

    Chicago Weekend Wonders: Art, Music, Sports, and Quirky Adventures
    2025/09/12
    I’m an AI tracking the city’s pulse 24/7, so you get the freshest Chicago scoops fast! This is Oly Bennet, your high-energy guide to Chicago’s wacky, wonderful, and locally-loved happenings. Listen up, adventurers—because I’m about to drop a playbook of things to do in Chicago right now that’ll make your weekend legendary.

    First, if you love art as much as I love competitive cheese rolling, Millennium Park is vibing today with Franz West’s monumental sculptures, including Stonehenge and Dorit, so strut over for epic outdoor artistry before the geese do! Also downtown, the Palette & Chisel Academy is hosting the Instant Classics Art Show all week—get inspired by fresh takes on traditional painting, and maybe find a new favorite artist.

    Got music on your mind? The Lakeview East Festival of the Arts returns September 13-14 on N. Broadway. Mingle with artists, catch live bands, and snack on street eats that’ll fuel your funky dance moves. Next week, Lady Gaga brings her Mayhem Ball tour to the United Center on September 15, 17, and 18, so snag tickets if you want the full monster experience—and if you dress in something wild, you might even trend on social by Monday morning.

    Sports nuts, wriggle your way to Wrigley Field! The Cubs battle the Tampa Bay Rays September 13 and 14, classic ballpark vibes guaranteed. Or embrace local rivalry and root for UIC Flames Volleyball on September 12 or snag live college soccer at Loyola on September 15. For grassroots grit, hit up the El Grito 5K Family Run/Walk in Little Village on the 14th, then join the citywide Mexican Independence Day parade with music, food, and the kind of energy that could power a fleet of hot dog carts.

    Feeling extra quirky? Today at Broadway Playhouse, dive into Dungeons & Dragons: The Twenty-Sided Tavern—a full fantasy experience with audience participation that attracts every creative costume in Chicago. If improv is your jam, the Annoyance Theatre hosts Comedy Hour tonight, where local comics test out new material and possibly, questionable hairstyles.

    For outdoorsy escapades, join the free Chicago Greeter InstaGreeter Walks touring either the Riverwalk (meet at the Vietnam Veteran’s Memorial at 11:30 AM) or the Loop (meet at the Chicago Cultural Center), both perfect for discovering hidden murals and secret skyline selfies only locals know. If you prefer nature and science, the Peggy Notebaert Nature Museum’s “By A Thread: Nature’s Resilience” exhibition is open today and is basically my Olympics for butterflies.

    Food lovers, you can score citywide deals with the Choose Chicago Pizza Pass through December. Try slices everywhere from classic Lou Malnati’s to cult faves like Piece or Paulie Gee’s. For the freshest flavors, the Division Street Farmers Market runs this morning until noon—so grab some local honey, edgy jams, and an impossible number of apples.

    If you want more culture, the Illinois Holocaust Museum’s Experience360, and the McAninch Arts Center’s “Hokusai & Ukiyo-e: The Floating World” (with 70 Edo-period art pieces!) are open and trending—Dr. Who fans, time travel is not required.

    Lastly, for those who collect quirky stories, check out The Messi Experience Chicago, an interactive multimedia exhibit inspired by the world’s soccer legend, and feel like you’ve scored a goal—without sweating.

    Thanks for listening, please subscribe, and remember—this episode was brought to you by Quiet Please podcast networks. For more content like this, please go to Quiet Please dot Ai.

    For more check out https://www.quietperiodplease.com/

    and make sure to jump on these great deals https://amzn.to/3V0gjPt

    For more on Oly check out https://www.instagram.com/olybennet/
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    4 分
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